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Saponarin

Saponarin is a flavone glucoside. It is found in Saponaria officinalis and in Strongylodon macrobotrys where it imparts the characteristic jade color to the flower. This coloration has been shown to be an example of copigmentation, a result of the presence of malvin (an anthocyanin) and saponarin in the ratio 1:9. Under the alkaline conditions (pH 7.9) found in the sap of the epidermal cells, this combination produced a blue-green pigmentation; the pH of the colorless inner floral tissue was found to be lower, at pH 5.6. Experiments showed that saponarin produced a strong yellow colouring in slightly alkaline conditions, resulting in the greenish tone of the flower.[1] It is also found in passion flowers (Passiflora sp.).

Saponarin
Names
IUPAC name
5-Hydroxy-6-(β-D-glucopyranosyl)-7-(β-D-glucopyranosyloxy)flavone
Systematic IUPAC name
5-Hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names
Isovitexin-7-O-glucoside
Saponaretin-7-O-glucoside
Identifiers
  • 20310-89-8 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 390121
  • 441381
UNII
  • 3081Z76OX9 Y
  • DTXSID10174201
  • InChI=1S/C27H30O15/c28-7-15-19(32)22(35)24(37)26(40-15)18-14(41-27-25(38)23(36)20(33)16(8-29)42-27)6-13-17(21(18)34)11(31)5-12(39-13)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2/t15-,16-,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
    Key: HGUVPEBGCAVWID-KETMJRJWSA-N
  • InChI=1/C27H30O15/c28-7-15-19(32)22(35)24(37)26(40-15)18-14(41-27-25(38)23(36)20(33)16(8-29)42-27)6-13-17(21(18)34)11(31)5-12(39-13)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2/t15-,16-,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
    Key: HGUVPEBGCAVWID-KETMJRJWBK
  • c1cc(ccc1c2cc(=O)c3c(o2)cc(c(c3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
Properties
C27H30O15
Molar mass 594.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

References edit

  1. ^ Greenish blue flower colour of Strongylodon macrobotrys. Kosaku Takeda, Aki Fujii, Yohko Senda and Tsukasa Iwashina, Biochemical Systematics and Ecology, Volume 38, Issue 4, August 2010, Pages 630–633, doi:10.1016/j.bse.2010.07.014

saponarin, flavone, glucoside, found, saponaria, officinalis, strongylodon, macrobotrys, where, imparts, characteristic, jade, color, flower, this, coloration, been, shown, example, copigmentation, result, presence, malvin, anthocyanin, saponarin, ratio, under. Saponarin is a flavone glucoside It is found in Saponaria officinalis and in Strongylodon macrobotrys where it imparts the characteristic jade color to the flower This coloration has been shown to be an example of copigmentation a result of the presence of malvin an anthocyanin and saponarin in the ratio 1 9 Under the alkaline conditions pH 7 9 found in the sap of the epidermal cells this combination produced a blue green pigmentation the pH of the colorless inner floral tissue was found to be lower at pH 5 6 Experiments showed that saponarin produced a strong yellow colouring in slightly alkaline conditions resulting in the greenish tone of the flower 1 It is also found in passion flowers Passiflora sp Saponarin NamesIUPAC name 5 Hydroxy 6 b D glucopyranosyl 7 b D glucopyranosyloxy flavoneSystematic IUPAC name 5 Hydroxy 2 4 hydroxyphenyl 6 2S 3R 4R 5S 6R 3 4 5 trihydroxy 6 hydroxymethyl oxan 2 yl 7 2S 3R 4S 5S 6R 3 4 5 trihydroxy 6 hydroxymethyl oxan 2 yl oxy 4H 1 benzopyran 4 oneOther names Isovitexin 7 O glucosideSaponaretin 7 O glucosideIdentifiersCAS Number 20310 89 8 Y3D model JSmol Interactive imageChemSpider 390121PubChem CID 441381UNII 3081Z76OX9 YCompTox Dashboard EPA DTXSID10174201InChI InChI 1S C27H30O15 c28 7 15 19 32 22 35 24 37 26 40 15 18 14 41 27 25 38 23 36 20 33 16 8 29 42 27 6 13 17 21 18 34 11 31 5 12 39 13 9 1 3 10 30 4 2 9 h1 6 15 16 19 20 22 30 32 38H 7 8H2 t15 16 19 20 22 23 24 25 26 27 m1 s1Key HGUVPEBGCAVWID KETMJRJWSA NInChI 1 C27H30O15 c28 7 15 19 32 22 35 24 37 26 40 15 18 14 41 27 25 38 23 36 20 33 16 8 29 42 27 6 13 17 21 18 34 11 31 5 12 39 13 9 1 3 10 30 4 2 9 h1 6 15 16 19 20 22 30 32 38H 7 8H2 t15 16 19 20 22 23 24 25 26 27 m1 s1Key HGUVPEBGCAVWID KETMJRJWBKSMILES c1cc ccc1c2cc O c3c o2 cc c c3O C H 4 C H C H C H C H O4 CO O O O O C H 5 C H C H C H C H O5 CO O O O OPropertiesChemical formula C27H30O15Molar mass 594 52 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesReferences edit Greenish blue flower colour of Strongylodon macrobotrys Kosaku Takeda Aki Fujii Yohko Senda and Tsukasa Iwashina Biochemical Systematics and Ecology Volume 38 Issue 4 August 2010 Pages 630 633 doi 10 1016 j bse 2010 07 014 nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Saponarin amp oldid 1153538350, wikipedia, wiki, book, books, library,

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